Proposal & Engagement Trips in Massachusetts

11 boats available

The best out of 11 deals in Massachusetts - enter dates to check availability

Top Proposal & Engagement Trips in Massachusetts

What boaters said about Proposal & Engagement Trips

  • 5.0
    /5
    (3 Hour Sunset Sail with a meal.)

    Awesome experience

    Captain Rick and Deb were wonderful hosts aboard the Artemis. It was a lovely day of sailing paired with a delicious lunch. Couldn’t have asked for a better experience!
    Amy A.
    Amy A.
    Reviewed on Sep 21, 2026
  • 5.0
    /5
    (4 Hour – Sail Around The Bay)

    Fun time with great people

    Captains Lynne and Mason were very engaging and willing to expertly answer all of our questions about sailing. thisnis a great experience!
    Peter M.
    Peter M.
    Reviewed on Sep 20, 2026
  • 5.0
    /5
    (2 Hour – Island Tour)

    Can’t wait for next time!

    We had the best time on our harbor cruise with Captain Paul and Alex! They were friendly, fun and very accommodating. They shared some fun facts along the ride but also let us do our thing, including control the music. Would 100% recommend them to anyone and look forward to the next occassion I have to book a trip.
    Brittany C.
    Brittany C.
    Reviewed on Sep 13, 2026
  • 5.0
    /5
    (5 Hr – Beach & Boat Tour)

    Birthday Trip

    My friends and I had a great time celebrating my birthday. The Cap. knows a lot of great palces to go. He is super nice!
    Savanna B.
    Savanna B.
    Reviewed on Sep 8, 2026
  • 5.0
    /5
    (2 Hr – Sunset/Cocktail Cruise)

    Great trip!

    Captain Ted was a great guide and we have a wonderful afternoon on the water! It’s was a beautiful spot and even got to fish! Great day!
    Amanda B.
    Amanda B.
    Reviewed on Sep 6, 2026